The instant invention relates to polyhydrodimethylnaphthalene spirofuran derivatives defined according to the structure: ##STR2## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond and uses of same in augmenting, enhancing or imparting an aroma of or to perfume compositions, perfumed articles and colognes.
Inexpensive chemical compounds which can provide strong persistent ambergris, ambery, tobacco, woody and animalic aromas, with woody, ambergris, sweet and cigar box-like topnotes are highly desirable in the art of perfumery. Many of the natural materials which provide such fragrances and contribute such desired nuances to perfume compositions as well as perfumed articles are high in cost, unobtainable at times, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
There is accordingly, a continuous effort to find synthetic materials which will replace, enhance or augment the fragrance notes provided by natural essential oils or compositions thereof. Unfortunately, many of the synthetic materials either have the desired nuances only to a relatively small degree or they contribute undesirable or unwanted odor to the compositions.
Of particular importance are odorants of the amber type in perfumery.
Enninga, et al, U.S. Pat. No. 3,045,028 issued on Jul. 17, 1962 discloses a number of polymethyl polyhydronaphthofurans, with some of such materials having an amber aroma and others having no amber aroma. Thus, Enninga, et al states that the compound having the structure: ##STR3## has no amber character but has an odor of the woody type. Enninga, et al further states that the compounds having the structures: ##STR4## do have amber aromas wherein, in the compound having the structure: ##STR5## R.sub.1 and R.sub.2 each represent methyl or hydrogen with at least one of R.sub.1 and R.sub.2 being methyl. Enninga, et al further discloses the compounds having the structures: ##STR6## (where one of the dashed lines represents a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds) as an intermediate in preparing perfumery compounds. By means of a process closely similar to that of Enninga, et al, Chodroff in U.S. Pat. No. 3,417,107 discloses the preparation of the compounds having the structures: ##STR7## wherein, one of the dashed lines represents a carbon-carbon double bond and each of the other of the dashed lines in each of the compounds represent carbon-carbon single bonds.
Chodroff, et al in U.S. Pat. No. 3,417,107 discloses that such compounds have ambergris-type aromas and also states that such compounds have high degrees of persistence. Nevertheless, compounds having high substantivity, and relatively high strengths in the ambergris area are lacking in commerce.
The compounds of our invention defined according to the generic structure: ##STR8## which covers the two compounds, to wit: ##STR9## have degrees of persistence approximately three-fold that of the compounds of the prior art and have strengths approximately three-fold that of the prior art (in the ambergris area). Thus, the compounds of our invention, the polyhydrodimethylnaphthalene spirofuran derivatives of our invention, have unexpected, unobvious and advantageous utilities when compared with compounds having similar structures in the prior art.
Indeed, other compounds of the prior art have vastly different aromas from the polyhydrodimethylnaphthalene spirofuran derivatives of our invention, to wit:
the compound having the structure: ##STR10## of Blumenthal, et al, U.S. Pat. No. 3,281,432; and the compounds of Sprecker, et al having the structure: ##STR11## of U.S. Pat. No. 4,639,330 wherein, one of R.sub.1 or R.sub.2 is hydrogen and the other of R.sub.1 or R.sub.2 is methyl and wherein, R.sub.3 represents C.sub.3 -C.sub.4 alkyl.
Our invention also relates to intermediates useful in preparing the polyhydrodimethylnaphthalene spirofuran derivatives of our invention, defined according to the structures: ##STR12##
A compound similar to the compound having the structure: ##STR13## is disclosed by Jacobson, Tetrahedron Letters, Vol. 21(13), pages 1205-1208 (1980) in a paper entitled "Three Carbon Annelation Reagents: Unsaturated Alpha Aminonitriles As Homoenolate Equivalents". Jacobson discloses the compound having the structure: ##STR14## which is somewhat related to the intermediate of our invention having the structure: ##STR15##
Furthermore, other spironaphthalene derivatives are known in the prior art but their structures and properties are totally distinct from the structures and properties of the polyhydrodimethylnaphthalene spirofuran derivatives of our invention. Thus, Hall, et al, U.S. Pat. No. 4,010,286 discloses the organoleptic utilites of the compounds having the structures: ##STR16## wherein, one of the dashed lines in the mixture of compounds defined according to the structure: ##STR17## is a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds.